Vanessa Trump Looks That Seriously Missed The Mark

Vanessa Trump strikes us as the type of woman who's most comfortable in jeans and a T-shirt. For example, when Tiger Woods confirmed his relationship with Trump in March 2025, he posted photos of him and Donald Trump Jr.'s ex looking happily coupled-up. In the now-viral post, she's wearing a white tank and dark denim. When daughter Kai Trump posts pics of mom Vanessa on social media, they usually show the mother-of-five wearing some variation of this casual uniform of jeans and a tee (except when Kai exposed her mother's worst style crime of all time).

But sometimes this uniform hasn't served her well. On one more than one occasion, the jeans and tee combo has delivered a fashion fail for Vanessa Trump. And then there are fancier occasions when her looks have seriously missed the mark as well. Though Trump's aesthetic seems more on point since she and Donald Jr. divorced in 2018, there are a few moments from her fashion past that we hope she doesn't repeat.

Vanessa Trump has opted for various shades of blue on many past red carpets. And it's a good choice for her; it looks nice with her coloring, and makes her stand out in a sea full of black dresses. The dress she wore in 2003, when she was still Vanessa Haydon and before she married Donald Trump Jr., should have been a winner. It draped beautifully off the shoulder and flaunted her toned back.

This look missed the mark, however, thanks to its material. Natural fabrics, such as silk and linen, are the worst culprits for wrinkling. Short of getting her dress steamed in the bathroom, Trump had no hope of recovering from this creasing. Also, her structured black bag, which is on the large side for a red carpet event, didn't work with the gown. A lighter bag, in a metallic or neutral shade, would have complemented the look better.

Vanessa Trump seemed to run in elite circles through her Manhattan upbringing, and was no stranger to leaning into the limelight in her relationships, though she doesn't appear to have a type (she was even attached to Leonardo DiCaprio in 1998). When she began dating Donald Trump Jr., she continued to mingle with N.Y.C.'s hoi polloi. But even this exposure to upper echelon living didn't mean she always dressed appropriately.

Case in point: This casual ensemble she wore to a viewing party of her boyfriend's hit show, "The Apprentice II" in 2004. Other guests were more dressed up, including Trump Jr., who donned a suit. Other women were in dresses and heels. Vanessa Trump's outfit — taupe jeans, white T-shirt, cranberry jacket, and designer satchel — wasn't necessarily bad. It just missed the mark because it wasn't appropriate for the occasion. In fact, we almost wonder if it showed a bit of disregard for her then-boyfriend that she couldn't bother getting more dressed up for the occasion.

After marrying Donald Trump Jr. in 2005, Vanessa Trump continued to run in fashion circles. While most people sitting front row at fashion shows try to put their best foot forward, that was not the case with Trump at the February 2006 Carlos Miele fashion show held during New York Fashion Week. This wasn't even a stylish enough outfit to be sitting in the last row. It looked more appropriate for the nosebleeds at a Britney Spears concert. The fitted tank with sparkly detail was paired with jeans that somehow gave her incredible body a slight muffin top. Add in boots worn over the skinny jeans, and it all screams 2006. And why the deep black boots? They don't look right with the rest of the look, throwing it out of balance.

Thankfully, Vanessa Trump has had a stunning transformation, and perhaps has enlisted a stylist to help her look appropriate for the big events that she's attended through the years, including the presidential inaugurations.

Vanessa Trump gave birth to her first child, Kai Trump, in May 2007. A year later, she hit the red carpet while attending the annual Operation Smile gala in N.Y.C. Unfortunately, everything about her look for the event felt off and somewhat Trump-ified. Before she married Donald Trump Jr., Vanessa looked more wholesome and polished; after the marriage, she looked more overdone, her hair was bleached, and she looked a bit tackier.

Like in this instance. The silver dress looked cheap, and satin like this can be particularly unforgiving when it comes to figure-flattery, as it catches every curve and accentuates it. Her blush was too heavy, as was the eye concealer, which was a shade too light, making her look like a fawn in headlights. Then there are the roots of the peroxided hair; while roots showing is no biggie these days, when there's a harsh strip like this, it's jarring. There's also something about her posture that makes Trump look like she's uncomfortable. This is one more example where we can see why she's a jeans and T-shirt kinda girl; casual just suits her better.

In September 2010, Vanessa and Donald Trump Jr. were parents of two (Donny was born in February 2009, and their third child, Tristan, wouldn't arrive for another 13 months). So the parents didn't have any newborns or kids on the way and hit the town. This time it was for another Operation Smile event, held in Beverly Hills, CA. And it was a gala. That's right, a gala. Where you get dressed up in formalwear. Like a gown. Not an oversized, unflattering tunic and black pants.

Hopefully, as Tiger Woods' girlfriend, she won't find herself required to attend too many formal events, because clearly she doesn't always have it in her to put the effort forward to dress up for fancy occasions. Cheering at the 18th hole, whether it's for Woods or golfing daughter Kai, seems much more up her fashion alley.